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WO1999043667A1 - Nouveaux pro-parfums cycliques ayant des taux variables de liberation de l'alcool de substance brute de fragrance - Google Patents

Nouveaux pro-parfums cycliques ayant des taux variables de liberation de l'alcool de substance brute de fragrance Download PDF

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Publication number
WO1999043667A1
WO1999043667A1 PCT/US1999/002732 US9902732W WO9943667A1 WO 1999043667 A1 WO1999043667 A1 WO 1999043667A1 US 9902732 W US9902732 W US 9902732W WO 9943667 A1 WO9943667 A1 WO 9943667A1
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Prior art keywords
substituted
unsubstituted
alkenyl
alkyl
pro
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PCT/US1999/002732
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English (en)
Inventor
Greg Scot Miracle
Kenneth Price Price
Lon Montgomery Gray
Original Assignee
The Procter & Gamble Company
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Application filed by The Procter & Gamble Company filed Critical The Procter & Gamble Company
Priority to EP99906824A priority Critical patent/EP1056739B1/fr
Priority to DK99906824T priority patent/DK1056739T3/da
Priority to DE69907420T priority patent/DE69907420T2/de
Priority to JP2000533424A priority patent/JP2002504548A/ja
Priority to US09/622,888 priority patent/US6544945B1/en
Priority to BR9908219-5A priority patent/BR9908219A/pt
Priority to CA002322511A priority patent/CA2322511A1/fr
Publication of WO1999043667A1 publication Critical patent/WO1999043667A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H9/00—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical
    • C07H9/02—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical the hetero ring containing only oxygen as ring hetero atoms
    • C07H9/04—Cyclic acetals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D317/34—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
    • C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
    • C07D319/08—1,3-Dioxanes; Hydrogenated 1,3-dioxanes condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0069—Heterocyclic compounds
    • C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms

Definitions

  • the present invention relates to cyclic pro-perfumes capable of releasing at least one fragrance raw material alcohol, preferably a tertiary fragrance raw material alcohol.
  • the novel pro-perfumes of the present invention can be modified by the formulator to control the rate at which the fragrance raw material alcohol is released once the material is applied, for example, to human skin.
  • fragrance raw materials Many modern fragrances are no longer derived from natural sources but are synthesized by modern chemical methods as highly pure fragrance raw materials (FRM). These FRM's are currently formulated to produce fine perfumes, colognes, eau de toilettes, after-shave lotions, and other personal fragrance compositions. Those skilled in the art of preparing these fragrance-containing compositions have categorized fragrances into three types based on their relative volatility; top, middle, and base notes.
  • Top, middle, and base notes each serve a different purpose in the blending of fragrances and when properly formulated produce a "balanced fragrance" composition. Based on volatility, these notes are described by those skilled in the art as: the base notes having the most long lasting aroma; the middle notes, have a 2
  • fragrance-containing composition Key to successfully formulating a fragrance-containing composition is the precise balance between these three groups of materials producing a fragrance-containing composition that diffuses during its evaporation in a manner which has an aesthetic quality.
  • fragrance raw materials especially fragrance raw material alcohols
  • formulators have not been able to well control the rate at which fragrance raw materials, especially fragrance raw material alcohols, are released when applied, for example, on human skin, hair, etc. Therefore, there has been a long felt need for a means of releasing at least one fragrance raw material alcohol, preferably tertiary alcohols, at a controllable rate.
  • the novel cyclic pro-perfumes which are the subject matter of the present invention, can not only release fragrance raw material alcohols but can be modified to release said alcohols within a range of time desirable to the formulator.
  • the cyclic pro-perfumes described herein are capable of delivering highly desirable tertiary alcohols.
  • the present invention meets the aforementioned needs in that it has been surprisingly discovered than certain cyclic pro-perfumes can be modified to release their fragrance raw material alcohols at variable rates after being exposed to an acid milieu wter alia human skin.
  • a first aspect of the present invention relates to cyclic pro-perfumes capable of releasing at least one fragrance raw material alcohol, said pro-perfumes having the formula:
  • R' O R 5 5 R 4 wherein -OR is a unit derived from a fragrance raw material alcohol;
  • R 1 is hydrogen, C ⁇ -C 2 alkyl, C]-C 22 alkenyl, C ⁇ -C ⁇ 2 aryl, C ⁇ -C 22 alkylenearyl, C 3 -C 20 substituted or unsubstituted alkyleneoxyalkyl, and mixtures thereof;
  • R 2 , R 3 , R 4 , and R 5 are each independently selected from hydrogen, C ⁇ -C 3 o substituted or unsubstituted linear alkyl, C 3 -C 0 substituted or unsubstituted branched alkyl, C 3 -C 3 o substituted or unsubstituted cyclic alkyl, C -C 30 substituted or unsubstituted linear alkenyl, C 3 -C 3 o substituted or unsubstituted branched alkenyl, C 3 -C 30 substituted or unsubstituted
  • the present invention also relates to fine fragrance compositions inter alia perfumes, colognes, after shaves, and eau de toilettes comprising said cyclic pro- perfumes.
  • personal care and personal hygiene articles may comprise the cyclic pro-perfumes described herein.
  • Non-limiting examples of these personal care items include deodorants, body lotions or creams, sun tan lotions, and shampoos.
  • the present invention also relates to a fragrance delivery system which comprises at least one cyclic pro-perfume as described herein.
  • a fragrance delivery system which comprises at least one cyclic pro-perfume as described herein.
  • said fragrance delivery system delivers at least one tertiary fragrance raw material alcohol.
  • the present invention relates to cyclic pro-perfumes capable of releasing at least one fragrance raw material alcohol.
  • the cyclic pro-perfumes of the present invention are capable of releasing in a controlled manner desirable tertiary 5
  • perfume raw material alcohols inter alia linalool, ethyllinalool, dihydromyrcenol, and tetrahydrolinalool.
  • the pro-perfumes of the present invention are essentially orthoesters.
  • Orthoesters in general, may be considered to be "acetals" of carboxylic acid esters which can be formed by the reaction of an ester with two equivalents of alcohol. Treatment of orthoesters with sufficient acid catalyst in the presence of moisture results in the "reversion” of orthoesters back into a mixture of ester and alcohol.
  • the ester alcohol is not the same as the orthoester forming alcohol, and depending upon the structure and reactivity of the orthoester components, one of the alcohols released from the reversion reaction may be the original ester alcohol resulting in one of the "orthoester forming" alcohols now comprising the ester. In this instance, "transesterification" has occurred.
  • the release rate of the fragrance raw material alcohol from the cyclic orthoesters of the present invention may be controlled, for example, by adjusting, separately or in combination, either the relative basicity of the orthoester oxygen atoms in the cyclic moiety or the torsional ring strain of the resulting cyclic orthoesters.
  • One result of these adjustments is to provide increased or decreased ring opening kinetics and thereby a means for regulating the release rate of the fragrance raw material alcohol.
  • cyclic pro-perfumes of the present invention have the formula:
  • fragrance raw material alcohol having the general formula ROH.
  • fragrance raw material alcohols which can be suitably released by the cyclic pro-perfumes of the present invention include 2,4-dimethyl-3-cyclohexene-l-methanol (Floralol), 2,4-dimethyl cyclohexane methanol (Dihydro floralol), 5,6-dimethyl-l-methylethenylbicyclo-[2.2.1]hept-5-ene- 6
  • Preferred fragrance raw material alcohols are tertiary alcohols / «ter alia 3,7- dimethyl-l,6-octadien-3-ol (linalool), 3,7-dimethyloctan-3-ol (tetrahydrolinalool), 3,7-dimethyl-l,6-nonadien-3-ol (ethyllinalool), and 2,6-dimethyl-7-octen-2-ol (dihydromyrcenol) .
  • R 1 is hydrogen, C C 2 alkyl, C ⁇ -C 22 alkenyl, C 6 -C ⁇ 2 aryl, C 6 -C 22 alkylenearyl, C 3 -C 2 o substituted or unsubstituted alkyleneoxyalkyl, and mixtures thereof.
  • R 1 is hydrogen, C ⁇ -C 4 alkyl, C 7 -C ⁇ 0 alkylenearyl; more preferably hydrogen, methyl, ethyl, propyl, iso-propyl, t-butyl, phenyl, substituted phenyl, benzyl and substituted benzyl.
  • R 2 , R 3 , R 4 , and R 5 are each independently hydrogen, C ⁇ -C 30 substituted or unsubstituted linear alkyl, C 3 -C 3 o substituted or unsubstituted branched alkyl, C 3 -C 3 o substituted or unsubstituted cyclic alkyl, C 2 -C 3 o substituted or unsubstituted linear alkenyl, C -C 3 o substituted or unsubstituted branched alkenyl, C 3 -C 3 o substituted or unsubstituted cyclic alkenyl, C 2 -C 3 o substituted or unsubstituted linear alkynyl, C 3 -C 3 o substituted or unsubstituted branched alkynyl, C ⁇ -C 3 o substituted or unsubstituted alkylenearyl, C6-C 30 substituted or unsubstituted aryl, C 2 -C
  • any two R 2 , R 3 , R 4 , or R 5 units can be taken together to form a fused ring cyclic pro-perfume having from 3 to 8 carbon atoms and optionally one or more heteroatoms in the ring.
  • An example of a fused ring cyclic pro-perfume includes the general formulae: RQ o and
  • the fused rings may also optionally comprise one or more heteroatoms, preferably oxygen, nitrogen, sulfur and mixtures thereof.
  • An example of a fused ring cyclic pro- perfume comprising a heteroatom has the formula:
  • R 8 is independently hydrogen, C ⁇ -C 22 alkyl, hydrogen, C ⁇ -C 3 o substituted or unsubstituted linear alkyl, C 3 -C 3 o substituted or unsubstituted branched alkyl, C 3 -C 30 substituted or unsubstituted cyclic alkyl, C -C 3 o substituted or unsubstituted linear alkenyl, C 3 -C 30 substituted or unsubstituted branched alkenyl, C 3 -C 30 substituted or unsubstituted cyclic alkenyl, C -C 30 substituted or unsubstituted linear alkynyl, C -C 30 substituted or unsubstituted branched alkynyl, C6-C 3 o substituted or unsubstituted alkylenearyl, C ⁇ -C 3 o substituted or unsubstituted aryl, C 2 -C 2 o substituted or unsubstitute
  • Non-limiting examples of saccharide units according to the present invention include erythrose, threose, arabinose, ribose, lysose, xylose, glucose, mannose, allose, altrose, talose, galactose, idose, gulose, fructose, and combinations thereof.
  • the saccharides of the present invention are preferably in the pyranose (closed ring) form, however, when in solution, an equilibrium may exist wherein some of the material may exist in the non- preferred ring opened form. Any number of saccharides can be linked together. For example, oligosaccharide - two or three saccharides or polysaccharides - more than three saccharides, are suitable for use in the present invention. 10
  • cyclic pro-perfumes of the present invention further comprise spiroannulated rings having from 3 to 8 carbon atoms and optionally one or more heteroatoms in the ring, examples of which have the general formulae:
  • fused ring or spiroannulated ring cyclic pro-perfumes may have their rings further substituted by one or more units, said units are independently hydroxyl, C ⁇ -C 2 alkoxy, C ⁇ -C 2 alkyl, C ⁇ -C 22 alkenyl, C ⁇ -C 12 aryl, C 6 -C 22 alkylenearyl units, and mixtures thereof.
  • the fused rings may also comprise one or more aromatic rings, including heteroaromatic rings. Examples of aromatic and heteroaromatic rings include benzene, naphthalene, pyridine, quinoline, isoquinoline, etc.
  • R 2 , R 3 , R 4 , and R 5 are selected such that said units comprise a vicinal diol or 1,3-type diol.
  • R 2 , R 3 , R 4 , and R 5 derive from diols non-limiting examples of which include 1,2- propanediol, 1,2- butanediol, 1,2-hexanediol, 1,2-octanediol, 1,3-hydroxyacetone, 1,3-octanediol. All of the preceding examples of diols include a hydroxy moiety at the terminus or the alkyl chain. However, as described herein below, non-terminal hydroxy diols are also preferred.
  • R 6 and R 7 are independently hydrogen (wherein the moiety -CR 6 R 7 - is a methylene unit), hydroxyl, nitro, nitrilo, C C 3 o substituted or unsubstituted linear alkyl, C 3 -C 3 o substituted or unsubstituted branched alkyl, C 3 -C 30 substituted or unsubstituted cyclic alkyl, C 2 -C 3 o substituted or unsubstituted linear alkenyl, C 3 -C 30 substituted or unsubstituted branched alkenyl, C -C 30 substituted or unsubstituted cyclic alkenyl, C 2 -C 3 o substituted or unsubstituted linear alkynyl, C 3 -C 30 substituted or unsubstituted branched alkynyl, C ⁇
  • R 6 and R 7 as described herein above can be taken together to form a spiroannulated ring or taken together with any R 2 , R 3 , R 4 , or R 5 unit to form-a fused ring, said spiroannulated or fused ring having from 3 to 8 carbons.
  • the resulting spiroannulated or fused rings may be further substituted by one or more Ci- C 22 alkyl, C ⁇ -C 2 alkenyl, C ⁇ -C ⁇ 2 aryl, C6-C 22 alkylenearyl units, and mixtures thereof.
  • n is an integer from 0 to 3, preferably 0 or 1, more preferably 0.
  • substituted or unsubstituted alkyleneoxy units are defined as moieties having the formula:
  • R ⁇ is hydrogen; R ⁇ is hydrogen, methyl, ethyl, and mixtures thereof; the index x is from 1 to about 20.
  • substituted or unsubstituted alkyleneoxyalkyl are defined as moieties having the formula:
  • R ⁇ is hydrogen, Cj-Cj g alkyl, C1-C4 alkoxy, and mixtures thereof; R ⁇ is hydrogen, methyl, ethyl, and mixtures thereof; the index x is from 1 to about 20 and the index y is from 2 to about 30.
  • substituted or unsubstituted alkylenearyl units are defined as moieties having the formula:
  • R ⁇ and R ⁇ are each independently hydrogen, hydroxy, C1 -C4 alkoxy, nitrilo, halogen, nitro, carboxyl (-CHO; -C0 2 H; -C0 2 R'; -CONH 2 ; -CONHR'; -CONR' 2 ; 12
  • R' is C ⁇ -C] linear or branched alkyl), amino, alkylamino, and mixtures thereof, p is from 1 to about 34.
  • substituted or unsubstituted aryloxy units are defined as moieties having the formula:
  • R ⁇ and R ⁇ are each independently hydrogen, hydroxy, C1-C4 alkoxy, nitrilo, halogen, nitro, carboxyl (-CHO; -C0 2 H; -C0 2 R'; -CONH 2 ; -CONHR'; -CONR' 2 ; wherein R' is Cj-C] 2 linear or branched alkyl), amino, alkylamino, and mixtures thereof.
  • substituted or unsubstituted alkyleneoxyaryl units are defined as moieties having the formula:
  • R ⁇ and R ⁇ are each independently hydrogen, hydroxy, C1-C4 alkoxy, nitrilo, halogen, nitro, carboxyl (-CHO; -C0 2 H; -C0 2 R'; -CONH 2 ; -CONHR'; -CONR' 2 ; wherein R' is Cj-C ⁇ 2 linear or branched alkyl), amino, alkylamino, and mixtures thereof, q is from 1 to about 34.
  • substituted or unsubstituted oxyalkylenearyl units are defined as moieties having the formula:
  • R ⁇ and R ⁇ are each independently hydrogen, hydroxy, C1 -C4 alkoxy, nitrilo, halogen, nitro, carboxyl (-CHO; -C0 2 H; -C0 R'; -CONH 2 ; -CONHR'; 13
  • R' is C]-C ⁇ 2 linear or branched alkyl), amino, alkylamino, and mixtures thereof, w is from 1 to about 34.
  • a formulator wishing to increase the degree of torsional strain in the pro-perfume ring may, however, select a diol having two non-terminus alcohols, for example, 2,3-octanediol or 3,4-octandiol.
  • the increase or decrease in the torsional strain of the cyclic pro-perfume ring provides the formulator with a means for adjusting the rate at which the fragrance raw material alcohol is released by the cyclic orthoester.
  • the two cyclic pro- perfumes having the formulae:
  • H 3 °CX O°R will exhibit different release rates of perfume raw material alcohol ROH due in part to the torsional strain provided by the eclipsing interaction of the methyl group with the alkyl chain. Fragrance Delivery System
  • the present invention further relates to fragrance delivery systems comprising: a) at least one cyclic pro-perfume; b) optionally one or more pro-perfumes, pro-fragrances, or pro-accords capable of releasing one or more fragrance raw materials, said fragrance raw materials selected from the group consisting of aldehydes, ketones, alcohols, esters, nitriles, nitro compounds, linear, branched and cyclic alkenes, ethers, and mixtures thereof; c) optionally one or more fragrance raw materials; and d) the balance carriers and adjunct ingredients.
  • pro-perfumes, pro-fragrances, or pro-accords which are combinable with the cyclic pro-perfumes of the present invention are preferably the pro-accords.
  • the term "accord” as used herein is defined as "a mixture of two or more 'fragrance raw materials' which are artfully combined to impart a pleasurable scent, odor, essence, or 14
  • pro-accord a material which is a "pro-accord” is capable of releasing a mixture of fragrance raw materials or a fragrance accord.
  • pro-accords and pro-fragrances include orthoesters, acetals, ketals, orthocarbonates, and the like described herein below.
  • the cyclic pro-perfumes of the present invention When formulated into a fragrance delivery system, will comprise from about 0.1% to about 99%, preferably from about 1% to about 50% by weight, of said fragrance delivery system.
  • the fragrance delivery systems of the present invention preferably comprise the pro-accords described herein below.
  • said pro-accords comprise singly or as an admixture from 0.1% to about 99%, preferably from about 1% to about 50% by weight of the fragrance delivery system.
  • the fragrance delivery systems of the present invention further comprises carriers, fixatives, and other adjunct ingredients which can be added in any suitable amount or ratio to the cyclic pro-perfumes or the optional pro-accords which comprise the balance of the delivery system.
  • Typical carriers are methanol, ethanol (preferred), iso-propanol, polyethylene glycol, as well as water in some instances.
  • Fixatives serve to lower the volatility of certain top and middle notes in order to extend their contact time on skin.
  • Adjunct ingredients include perfume raw material components which are essential oils and are therefore not a single chemical entity.
  • the adjunct ingredients may be mixtures of synthetic fragrance raw materials which serve a further purpose in addition to providing a pleasurable odor.
  • One class of preferred compounds useful as pro-accords according to the present invention are orthoesters having the formula:
  • R is hydrogen, Cj-Cg linear alkyl, C4- 20 branched alkyl, C6-C Q cyclic alkyl, Cg-C 2 o branched cyclic alkyl, C6-C 2 Q linear alkenyl, Cg-C 2 o branched alkenyl, Cg-C 2 o cyclic alkenyl, C6-C 2 o branched cyclic alkenyl, C6-C 2 o substituted or unsubstituted aryl, preferably the moieties which substitute the aryl units are alkyl moieties, and mixtures thereof, preferably R is hydrogen, methyl, ethyl, and phenyl.
  • Rl, R2 and R 3 are independently C ⁇ -C Q linear, branched, or substituted alkyl; C - C 2 o linear, branched, or substituted alkenyl; C5-C Q substituted or unsubstituted cyclic alkyl; C6-C 2 o substituted or unsubstituted aryl, C 2 -C40 substituted or unsubstituted alkyleneoxy; C3-C40 substituted or unsubstituted alkyleneoxyalkyl; C6-C40 substituted or unsubstituted alkylenearyl; C6 ⁇ C3 2 substituted or unsubstituted aryloxy; Cg-C4o substituted or unsubstituted alkyleneoxyaryl; C.5-C40 oxyalkylenearyl; and mixtures thereof.
  • substituted herein is meant "compatible moieties which replace a hydrogen atom".
  • substituents are hydroxy, nitrilo, halogen, nitro, carboxyl (-CHO; -C0 2 H; -C0 2 R'; - CONH 2 ; -CONHR'; -CONR' 2 ; wherein R' is Cj-C ⁇ linear or branched alkyl), amino, C]-C ⁇ 2 mono- and dialkylamino, and mixtures thereof.
  • Another class of compound useful as pro-accords according to the present invention are acetals and ketals having the formula:
  • R is Cj-C o linear alkyl, C4-C20 branched alkyl, Cg-C20 cyclic alkyl, C5- C 2 o branched cyclic alkyl, C ⁇ -C 2 o linear alkenyl, C6 ⁇ C 2 Q branched alkenyl, G6-C 2 o cyclic alkenyl, C6-C Q branched cyclic alkenyl, Cg-C 2 o substituted or unsubstituted aryl, preferably the moieties which substitute the aryl units are alkyl moieties, and mixtures thereof
  • Rl is hydrogen, R, or in the case wherein the pro-accord is a ketal, R and Rl can be taken together to form a ring.
  • R 2 and R 3 are independently selected from the group consisting of C5-C Q linear, branched, or substituted alkyl; C4-C 2 o linear, branched, or substituted alkenyl; C5-C 2 Q substituted or unsubstituted cyclic alkyl; Cg-C o substituted or unsubstituted aryl, C2-C40 substituted or unsubstituted alkyleneoxy; C3-C40 substituted or unsubstituted alkyleneoxyalkyl; C6-C40 substituted or unsubstituted alkylenearyl; C6-C32 substituted or unsubstituted aryloxy; C6-C40 substituted or unsubstituted alkyleneoxyaryl; C6-C40 oxyalkylenearyl; and mixtures thereof.
  • substituted herein is meant "compatible moieties which replace a hydrogen atom".
  • substituents are hydroxy, nitrilo, halogen, nitro, carboxyl (-CHO; -C0 2 H; -C0 2 R'; - CONH 2 ; -CONHR'; -CONR' 2 ; wherein R' is C1 -C 12 linear or branched alkyl), amino, C]-C ⁇ 2 mono- and dialkylamino, and mixtures thereof
  • orthocarbonates having the formula:
  • Non-limiting examples of substituents are hydroxy, nitrilo, halogen, nitro, carboxyl (-CHO; -C0 2 H; -C0 2 R'; - CONH 2 ; -CONHR'; -CONR' 2 ; wherein R' is C ⁇ -C 12 linear or branched alkyl), amino, C]-C ⁇ 2 mono- and dialkylamino, and mixtures thereof. Fragrance Release Half-life
  • the cyclic pro-perfumes and other pro-accords useful in the fragrance delivery systems of the present invention generally have a delayed release of final fragrance accord in order to achieve the increased fragrance longevity benefits described herein.
  • the pro-accords generally also deliver the fragrance accords during a time period useful to the formulator, for example, within a time period desirable to the consumer.
  • the pro-accords generally have a "Fragrance Release Half-life" of less than or equal to 12 hours when measured in NaH 2 P ⁇ 4 buffer at pH 2.5 and greater than or equal to 0.1 hour when measured in NaH 2 P ⁇ 4 buffer at pH 5.3.
  • the "Fragrance Release Half-life” is defined herein as follows. 18
  • Pro-accords deliver their corresponding mixture of fragrance raw materials or fragrance accords according to the equation:
  • Pro-Accord •*- Accord wherein the accord which is released may be a binary accord or a multiple fragrance raw material accord.
  • Rate k [Pro-accord] and can be further expressed by the formula:
  • the phosphate buffered water is prepared by admixing 3.95 mL of 85% phosphoric acid (H3PO4) and 24 g of sodium dihydrogen phosphate (NaH 2 P ⁇ 4) with one liter of water. The pH of this solution is approximately 2.5. Next 10 mL of the phosphate buffer is admixed with 90 mL of dioxane and the pro-fragrance to be analyzed is added. The hydrolysis kinetics are then monitored by conventional HPLC at 30° C. 19
  • the pro-accord component of the present invention in order to assure the stability of acid labile pro-accords, may include a source of reserve alkalinity-- equivalent to at least 0.001 molar (1 milli-molar) sodium hydroxide.
  • This reserve alkalinity generally serves to prevent premature release of the fragrance raw materials by the pro-accords prior to exposure of the pro-accords to skin.
  • a reserve alkalinity of at least 0.001 molar is defined as "the amount of alkaline material present in one liter of the second component when placed in an equivalent volume of water, would produce a hydroxide ion equivalent of 0.001 moles or greater".
  • 0.0004 g of NaOH present in a 10 mL aliquot of the second component would produce a reserve alkalinity of at least 0.001 molar.
  • Suitable sources of alkalinity are the alkali metal and alkali earth hydroxides.
  • other suitable sources of alkalinity can be used which are compatible with the pro-accords of the "pro-accord component".
  • fragrance delivery system of the present invention may be suitably use in a fine fragrance composition.
  • Said perfume compositions provide extended fragrance character impressions, and comprise: A) a pro-accord component comprising: i) from 0.1% to 99% by weight, of one or more pro-accords formed from at least one fragrance raw material, said pro- accord releasing upon hydrolysis at least two fragrance raw materials selected from the group consisting of primary, secondary, and tertiary alcohols, aldehydes, ketones, esters, carbonates, and mixtures thereof, provided each pro-accord: a) is formed from at least one fragrance raw material having a molecular weight greater than or equal to about lOO g/mol; b) has a molecular weight greater than or equal to about 300 g/mol; 20
  • c) has a molecular weight at least two times greater than the lowest molecular weight fragrance raw material which comprises said pro-accord; d) has a fragrance release half-life of less than or equal to about 12 hours at pH 2.5 or greater than or equal to about 0.1 hour at pH 5.3 when measured in NaH 2 P ⁇ 4 buffer; ii) the balance carriers, stabilizers, and other adjunct ingredients whereby said pro-accord component is provided with an amount of reserve alkalinity equal to at least 0.001 molar NaOH;
  • a fragrance raw material component comprising: i) from 0.1% to about 99% by weight, of a mixture of base note fragrances; ii) from 0.1% to about 99% by weight, of one or more top and middle note fragrances; ii) the balance carriers, fixatives, and other adjunct ingredients; and
  • a cyclic pro-perfume component comprising one or more of the cyclic pro-perfumes described herein.
  • EXAMPLE 1 6-tri-fl-acetvM,2-fethvHinalyl)orthoacetyl-ct-D-gl ⁇ copyranose Acetobromoglucose, tetrabutylammonium bromide (0.3 equiv), and ethyllinalool (3 equiv) are suspended in dry collidine and stirred at 65 °C for 3 days. The reaction mixture is diluted with 2 volumes of ether, washed twice with water, and then dried (MgS0 4 ), evaporated, and purified by flash chromatography.
  • the cyclic pro-perfumes of the present invention are also suitable for use in personal care and personal hygiene compositions.
  • the following are examples of a personnel cleanser composition which is prepared by combining the following ingredients using conventional mixing techniques.
  • Carbomer 954 2 0.250 0.250 0.250 0.250 0.250 0.250 0.250
  • Steareth-21 0.50 0.50 0.50
  • Examples 3-6 can be suitably prepared as follows.
  • the Phase A ingredients are mixed at room temperature to form a dispersion and heated with stirring to 70-80° C.
  • Phase B is heated with stirring to 70-80° C.
  • Phase B is then added to Phase A with mixing to form the emulsion.
  • Phase C is added to neutralize the composition.
  • the Phase D ingredients are added with mixing, followed by cooling to 45-50° C.
  • the Phase E ingredients are then added with stirring, followed by cooling to 40° C.
  • Phase F is heated with mixing to 40° C. and added to the emulsion, which is cooled to room temperature.
  • the resulting cleansing composition is useful for cleansing the skin.
  • the emulsion de-emulsifies upon contact with the skin.

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Abstract

Cette invention se rapporte à de nouveaux pro-parfums cycliques, représentés par la formule générale (I), où OR représente une fraction dérivée d'un alcool de substance brute de fragrance, de préférence un alcool tertiaire. Ces pro-parfums cycliques contiennent de préférence des orthoesters de glucosyle et de dioxolane, propres à libérer leur fragrance sur la peau humaine pendant une période plus longue, lorsqu'ils sont utilisés dans des parfums et des fragrances fines.
PCT/US1999/002732 1998-02-24 1999-02-08 Nouveaux pro-parfums cycliques ayant des taux variables de liberation de l'alcool de substance brute de fragrance WO1999043667A1 (fr)

Priority Applications (7)

Application Number Priority Date Filing Date Title
EP99906824A EP1056739B1 (fr) 1998-02-24 1999-02-08 Nouveaux pro-parfums cycliques ayant des taux variables de liberation de l'alcool de substance brute de fragrance
DK99906824T DK1056739T3 (da) 1998-02-24 1999-02-08 Hidtil ukendte cykliske pro-parfumer med modificeret frigivelseshastighed af duftstofråmaterialealkohol
DE69907420T DE69907420T2 (de) 1998-02-24 1999-02-08 Zyklische pro-duftverbindungen die die geruchrohstoffalkohol freisetzungsstufe ändern
JP2000533424A JP2002504548A (ja) 1998-02-24 1999-02-08 調整しうるフレグランス原料アルコール放出速度を有した新規な環式プロ香料
US09/622,888 US6544945B1 (en) 1998-02-24 1999-02-08 Cyclic pro-perfumes having modifiable fragrance raw material alcohol release rates
BR9908219-5A BR9908219A (pt) 1998-02-24 1999-02-08 Pró-perfumes cìclos tendo taxas de liberação de matéria-prima de álcool com fragrância modificável
CA002322511A CA2322511A1 (fr) 1998-02-24 1999-02-08 Nouveaux pro-parfums cycliques ayant des taux variables de liberation de l'alcool de substance brute de fragrance

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US7570898P 1998-02-24 1998-02-24
US60/075,708 1998-02-24

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US8919662B2 (en) 2004-06-24 2014-12-30 Enviroscent, Inc. Scent devices and methods
US9149552B1 (en) 2014-09-29 2015-10-06 Enviroscent, Inc. Coating providing modulated release of volatile compositions
WO2016096540A1 (fr) * 2014-12-17 2016-06-23 Henkel Ag & Co. Kgaa Orthoformiates utilisés comme précurseur de parfum
USD800286S1 (en) 2015-07-31 2017-10-17 Enviroscent, Inc. Collection of scent-infused wound sheets
US10596290B2 (en) 2015-06-09 2020-03-24 Enviroscent, Inc. Formed three-dimensional matrix and associated coating providing modulated release of volatile compositions
US10953125B2 (en) 2016-09-30 2021-03-23 Enviroscent, Inc. Articles formed of pulp base materials with modulated scent release

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WO2001091712A3 (fr) * 2000-06-01 2002-06-06 Procter & Gamble Systemes de diffusion de parfums a duree accrue dans lesquels le parfum initial n'est pas altere
US6610646B2 (en) 2000-06-01 2003-08-26 The Procter & Gamble Company Enhanced duration fragrance delivery system having a non-distorted initial fragrance impression
US7208463B2 (en) 2000-06-02 2007-04-24 The Procter & Gamble Company Fragrance compositions
US7208462B2 (en) 2000-06-02 2007-04-24 The Procter & Gamble Company Fragrance compositions
US7208464B2 (en) 2000-06-02 2007-04-24 The Procter & Gamble Company Fragrance compositions
US7407650B2 (en) 2000-10-27 2008-08-05 The Procter & Gamble Company Fragrance compositions
US7413731B2 (en) 2000-10-27 2008-08-19 The Procter And Gamble Company Fragrance compositions
US7041337B2 (en) 2000-11-03 2006-05-09 The Procter & Gamble Company Methods of fragrancing a surface
US7208465B2 (en) 2000-11-03 2007-04-24 The Procter & Gamble Company Methods and compositions for improved fragrancing of a surface
US9381266B2 (en) 2004-06-24 2016-07-05 Enviroscent, Inc. Scent devices and methods
US10286098B2 (en) 2004-06-24 2019-05-14 Enviroscent, Inc. Scent devices and methods
US8919662B2 (en) 2004-06-24 2014-12-30 Enviroscent, Inc. Scent devices and methods
WO2009030372A1 (fr) * 2007-09-03 2009-03-12 Merck Patent Gmbh Dérivés de dha bifonctionnels
DE102007041854A1 (de) 2007-09-03 2009-03-05 Merck Patent Gmbh Bifunktionelle DHA-Derivate
US9132204B2 (en) 2010-03-31 2015-09-15 Enviroscent, Inc. Methods, compositions and articles for olfactory-active substances
US9694096B2 (en) 2010-03-31 2017-07-04 Enviroscent, Inc. Methods compositions and articles for olfactory-active substances
US11167055B2 (en) 2010-03-31 2021-11-09 Enviroscent, Inc. Methods, compositions and articles for olfactory-active substances
WO2011123723A1 (fr) 2010-03-31 2011-10-06 Enviroscent, Inc. Procédés, compositions et articles pour substances actives sur le plan olfactif
US10987445B2 (en) 2010-03-31 2021-04-27 Enviroscent, Inc. Methods, compositions and articles for olfactory-active substances
US9149552B1 (en) 2014-09-29 2015-10-06 Enviroscent, Inc. Coating providing modulated release of volatile compositions
US10647868B2 (en) 2014-09-29 2020-05-12 Enviroscent, Inc. Coating providing modulated release of volatile compositions
US9694097B2 (en) 2014-09-29 2017-07-04 Enviroscent, Inc. Coating providing modulated release of volatile compositions
US11498095B2 (en) 2014-09-29 2022-11-15 Enviroscent, Inc. Coating providing modulated release of volatile compositions
WO2016096540A1 (fr) * 2014-12-17 2016-06-23 Henkel Ag & Co. Kgaa Orthoformiates utilisés comme précurseur de parfum
US9981937B2 (en) 2014-12-17 2018-05-29 Henkel Ag & Co. Kgaa Orthoformic acid esters as pro-fragrances
US10596290B2 (en) 2015-06-09 2020-03-24 Enviroscent, Inc. Formed three-dimensional matrix and associated coating providing modulated release of volatile compositions
US11241514B2 (en) 2015-06-09 2022-02-08 Enviroscent, Inc. Formed three-dimensional matrix and associated coating providing modulated release of volatile compositions
US12109340B2 (en) 2015-06-09 2024-10-08 Enviroscent, Inc. Formed three-dimensional matrix and associated coating providing modulated release of volatile compositions
USD800286S1 (en) 2015-07-31 2017-10-17 Enviroscent, Inc. Collection of scent-infused wound sheets
US10953125B2 (en) 2016-09-30 2021-03-23 Enviroscent, Inc. Articles formed of pulp base materials with modulated scent release
US11458222B2 (en) 2016-09-30 2022-10-04 Enviroscent, Inc. Articles formed of pulp base materials with modulated scent release
US11931487B2 (en) 2016-09-30 2024-03-19 Enviroscent, Inc. Articles formed of pulp base materials with modulated scent release

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DK1056739T3 (da) 2003-06-02
BR9908219A (pt) 2000-10-24
CA2322511A1 (fr) 1999-09-02
JP2002504548A (ja) 2002-02-12
US6544945B1 (en) 2003-04-08
AR018111A1 (es) 2001-10-31
DE69907420D1 (de) 2003-06-05
DE69907420T2 (de) 2004-03-11
CN1298400A (zh) 2001-06-06
ES2197620T3 (es) 2004-01-01
EP1056739A1 (fr) 2000-12-06

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